CN114304375A - Lipid composition - Google Patents

Abstract

The present invention provides improved methods for extracting and preparing lipids from biological sources for use in pharmaceuticals, nutraceuticals, and functional foods.

Description

Lipid composition

This application is a divisional application of a Chinese patent application with the application number of 201680016911.0 (international application number PCT/IB2016/000326), the filing date of February 10, 2016, and the invention name of "lipid composition".

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of US Provisional Patent Application No. 62/114,811, filed February 11, 2015, the contents of which are incorporated herein by reference in their entirety.

technical field

The present invention provides improved methods for extracting and preparing lipids from biological sources for use in pharmaceuticals, nutraceuticals, and functional foods, and compositions produced from the lipids.

Background technique

Krill oil is one of the fastest growing nutritional products. Krill oil can be extracted from any species of krill, but is most commonly extracted from Antarctic krill (Euphausia superba). Krill oil provides a biological source of omega-3 fatty acids such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) as well as the antioxidant astaxanthin. Krill oil is generally characterized by high levels of phospholipids and triglycerides.

WO2008/117062 describes the use of polar solvents to extract krill oil from krill meal and extraction methods such as supercritical fluid extraction. One problem with extracting krill oil from krill meal is that the oil typically has a high viscosity, which makes it difficult to formulate into preferred delivery forms such as gel capsules. The reason for the high viscosity has not been previously described.

WO2009/027692 and WO2010/097701 describe methods for preparing krill protein-lipid coagulum and extracting oil from the coagulum. The resulting oil can have a low viscosity. However, the coagulum can be difficult to store and transport due to high moisture content.

Very little work has been done to discover methods for extracting low viscosity krill oil from the more readily available krill meal. Therefore, there is a need in the art for methods for extracting low viscosity krill oil from krill meal and the low viscosity krill oil obtained by those methods.

SUMMARY OF THE INVENTION

The present invention provides improved methods for the extraction and preparation of lipids from biological sources for use in pharmaceuticals, nutraceuticals and functional foods.

Accordingly, in some embodiments, the present invention provides a desalinated krill lipid composition comprising: about 30% to 50% w/w phospholipids w/w and about 32% to 52% w/w triglycerides and wherein the composition has one or more of the following properties: a) the composition comprises about 3% w/w to 13% w/w free fatty acids; b) the composition comprises about 0.5% w/w to 5% w/w lysophospholipids; c) the composition comprises less than about 0.2% w/w inorganic salts; d) the composition comprises less than about 2 mg N/100g; e) the composition the composition comprises less than about 2 ppm Cu ⁺⁺ ; f) the composition comprises less than about 3 ppm total arsenic; g) the composition comprises from about 0.01% to about 1% w/w ethyl ester; h) the combination The composition is characterized by a conductivity of less than about 20 μS/cm when measured using 5% dry matter in 95% ethanol; i) the composition is characterized by a viscosity of about 100 to 400 mPas at 25°C; and ( j) The composition comprises from about 20 ppm to about 2000 astaxanthin esters. In some embodiments, the composition has 2 or more of properties (a) to (j). In some embodiments, the composition has 3 or more of properties (a) to (j). In some embodiments, the composition has 4 or more of properties (a) to (j). In some embodiments, the composition has 5 or more of properties (a) to (j). In some embodiments, the composition has 6 or more of properties (a) to (j). In some embodiments, the composition has 7 or more of properties (a) to (j). In some embodiments, the composition has 8 or more of properties (a) to (j). In some embodiments, the composition has 8 or more of properties (a) to (j). In some embodiments, the composition has all of properties (a) to (j). In some embodiments, the composition has at least properties (c) and (i). In some embodiments, the composition has at least property (h). In some embodiments, the composition has at least properties (e) and (f). In some embodiments, the composition has at least property (d). In some embodiments, the composition has at least properties (c), (d), (e), (f), (h) and (i).

In some embodiments, the present invention provides a krill phospholipid concentrate comprising: about 50% to 85% w/w phospholipids and about 5% to 35% w/w triglycerides; and wherein the composition has the following properties one or more of: (a) the composition comprises about 2% w/w to 13% w/w free fatty acids; (b) the composition comprises about 0.5% w/w to 10% w/w w lysophospholipids; (c) the composition comprises less than about 0.2% w/w inorganic salt; (d) the composition comprises less than about 2 mg N/100g; (e) the composition comprises less than about 2 ppm Cu ⁺⁺ ; (f) the composition comprises less than about 3 ppm total arsenic; (g) the composition comprises from about 0.01% to about 1% w/w ethyl ester; (h) the characteristics of the composition having a conductivity of less than about 20 μS/cm when measured using 5% dry matter in 95% ethanol; (i) the composition is characterized by having a viscosity at 35°C of about 600 to 1600 mPas; and (j) The composition contains less than about 100 ppm of astaxanthin esters. In some embodiments, the composition has 2 or more of properties (a) to (j). In some embodiments, the composition has 3 or more of properties (a) to (j). In some embodiments, the composition has 4 or more of properties (a) to (j). In some embodiments, the composition has 5 or more of properties (a) to (j). In some embodiments, the composition has 6 or more of properties (a) to (j). In some embodiments, the composition has 7 or more of properties (a) to (j). In some embodiments, the composition has 8 or more of properties (a) to (j). In some embodiments, the composition has 9 or more of properties (a) to (j). In some embodiments, the composition has all of properties (a) to (j). In some embodiments, the composition has at least properties (c) and (i). In some embodiments, the composition has at least property (h). In some embodiments, the composition has at least properties (e) and (f). In some embodiments, the composition has at least property (d). In some embodiments, the composition has at least properties (c), (d), (e), (f), (h) and (i).

In some embodiments, the present invention provides krill neutral lipid compositions comprising:

about 70% to 95% w/w triglycerides and about 2% to 20% w/w phospholipids; and wherein the composition has one or more of the following properties: (a) the composition comprises about 0.5 % w/w to 10% w/w free fatty acid; (b) the composition comprises about 0.1% w/w to 2% w/w lysophospholipid; (c) the composition comprises less than about 0.2% w /w of inorganic salts; (d) the composition contains less than about 2 mgN/100g; (e) the composition contains less than about 2 ppm Cu ⁺⁺ ; (f) the composition contains less than about 3 ppm total Arsenic; (g) the composition comprises from about 0.01% to about 1% w/w ethyl ester; (h) the composition is characterized as having less than about 20 μS when measured using 5% dry matter in 95% ethanol /cm of electrical conductivity; i) the composition is characterized by a viscosity of less than about 200 mPas at 25°C; j) the composition comprises greater than about 300 ppm of astaxanthin esters. In some embodiments, the composition has 2 or more of properties (a) to (j). In some embodiments, the composition has 3 or more of properties (a) to (j). In some embodiments, the composition has 4 or more of properties (a) to (j). In some embodiments, the composition has 5 or more of properties (a) to (j). In some embodiments, the composition has 6 or more of properties (a) to (j). In some embodiments, the composition has 7 or more of properties (a) to (j). In some embodiments, the composition has 8 or more of properties (a) to (j). In some embodiments, the composition has 9 or more of properties (a) to (j). In some embodiments, the composition has all of properties (a) to (j). In some embodiments, the composition has at least properties (c), (i) and (j). In some embodiments, the composition has at least property (h). In some embodiments, the composition has at least properties (e) and (f). In some embodiments, the composition has at least property (d). In some embodiments, the composition has at least properties (c), (d), (e), (f), (h), (i) and (j).

In some embodiments, the present invention provides a crude krill lipid composition comprising: about 30% to 50% w/w phospholipids w/w and about 26% to 46% w/w triglycerides; and wherein said The composition has one or more of the following properties: (a) the composition comprises about 1% w/w to 7% w/w triglycerides; (b) the composition comprises about 2% w/w w to 12% w/w free fatty acids; (c) the composition comprises about 1% w/w to 7% w/w cholesterol; (d) the composition comprises about 0.1% w/w to 2% w /w cholesteryl ester, more preferably about 0.2% w/w to about 1.0% w/w cholesteryl ester; (e) the composition comprises about 0.5% w/w to 5% w/w inorganic salt; (f) The composition comprises about 0.5% w/w to 5% w/w tertiary amine. In some embodiments, the composition has 2 or more of properties (a) to (f). In some embodiments, the composition has 3 or more of properties (a) to (f). In some embodiments, the composition has 4 or more of properties (a) to (f). In some embodiments, the composition has 5 or more of properties (a) to (f). In some embodiments, the composition has all of properties (a) to (f). In some embodiments, the composition has at least properties (a), (c) and (e).

In some embodiments, the present invention provides a concentrated krill astaxanthin composition comprising: about 400 to 4000 ppm of astaxanthin esters and greater than about 98% krill neutral lipids.

In some embodiments, the present invention provides an oral delivery vehicle comprising the composition described above. In some embodiments, the vehicle is a soft gel capsule. In some embodiments, the present disclosure provides a functional food, nutritional supplement, dietary supplement, or medical food comprising the composition described above. In some embodiments, the composition may include a second nutritional ingredient in addition to the krill lipid composition. In some embodiments, the present invention provides a pharmaceutically acceptable carrier and a krill lipid composition as described above.

definition

As used herein, "phospholipid" refers to an organic compound having two fatty acid moieties attached at the sn-1 and sn-2 positions of glycerol and containing a head group at the sn-3 position of glycerol linked by a phosphate residue . Exemplary head group moieties include choline, ethanolamine, serine, and inositol. Phospholipids include phosphatidylcholine, phosphatidylserine, phosphatidylethanolamine, phosphatidylinositol, and phosphatidic acid. A fatty acid moiety is a portion of a fatty acid molecule that is bound at the sn-1 or sn-2 position, eg, through an ester or ether bond. When the fatty acid moiety is a fatty acyl group, the aliphatic chain of the fatty acyl group is linked by an ester bond, and when the fatty acid moiety is an aliphatic chain of a fatty acid, the aliphatic chain is linked by an ether bond. When a specific fatty acid is mentioned in conjunction with a phospholipid of the invention (eg EPA or DHA), it should therefore be referred to as the relevant fatty acyl group or its aliphatic chain.

As used herein, the term "ether phospholipid" refers to a phospholipid in which the fatty acid moiety at one of the sn-1 or sn-2 positions is an aliphatic chain of fatty acids linked by ether linkages. Ether phospholipids include, for example, alkanoylphosphatidylcholines, alkanoylphosphatidylethanolamines, and alkanoylphosphatidylserines.

As used herein, the term "long-chain polyunsaturated fatty acid" refers to a fatty acid having 20 or more carbons and being unsaturated at two or more bonds.

As used herein, the term omega-3 fatty acid refers to a polyunsaturated fatty acid having a final double bond in the hydrocarbon chain between the third and fourth carbon atoms from the methyl end of the molecule. Non-limiting examples of omega-3 fatty acids include 5,8,11,14,17-eicosapentaenoic acid (EPA), 4,7,10,13,16,19-docosahexaenoic acid ( DHA) and 7,10,13,16,19-docosapentaenoic acid (DPA).

As used herein, the term "physiologically acceptable carrier" refers to any carrier or excipient commonly used with oily pharmaceuticals. Such carriers or excipients include, but are not limited to, oils, starches, sucrose and lactose.

As used herein, the term "oral delivery vehicle" refers to any means of oral delivery of a drug, including but not limited to capsules, pills, tablets, and syrups.

As used herein, the term "food product" refers to any food or feed suitable for consumption by humans, non-ruminants or ruminants. A "food product" can be a prepared and packaged food (eg, mayonnaise, salad dressing, bread or cheese) or animal feed (eg, extruded or pelleted animal feed or roughage). "Prepared food product" means any prepackaged food approved for human consumption.

As used herein, the term "foodstuff" refers to any substance suitable for human or animal consumption.

As used herein, the term "functional food" refers to a food product to which a biologically active supplement has been added.

As used herein, the term "infant food" refers to food products such as milk formula formulated for infants.

As used herein, the term "senior food" refers to a food product formulated for the elderly.

As used herein, the term "maternity food" refers to food products formulated for pregnant women.

As used herein, the term "nutrient supplement" refers to a food product formulated as a dietary or nutritional supplement for use as part of the diet.

As used herein, unless otherwise indicated, the term w/w (weight/weight) is based on the amount of a given substance in the composition by weight and is expressed as a percentage of the total composition. For example, a composition comprising 50% w/w phospholipids means that the mass of phospholipids is 50% of the total mass of the composition (ie, 50 grams of phospholipids in 100 grams of a composition such as an oil). When specifying solvent concentrations throughout the specification, the concentration refers to the weight percent of the solvent in the specified solvent solution. As a non-limiting example, 96% ethanol comprises 96% ethanol and 4% water. As another non-limiting example, when the specification describes a lipid solution as containing 20% w/w dry matter and the solvent is 95% ethanol, this means that 100 g of the solution contains a total of 20 grams of dry matter and 80 g of 95% Ethanol.

As used herein, the term "krill meal" refers to a dry powder prepared from krill and having a moisture content of from about 3% to about 15%.

Detailed ways

The present invention provides improved methods for extracting and preparing lipids from biological sources for use in nutraceuticals, pharmaceuticals, and functional foods, and compositions produced from the lipids. In a particularly preferred embodiment, the biological source is krill, such as Antarctic krill or Pacific krill (Euphausia paciflca).

One of the main problems with existing krill oils is that the oils are viscous and difficult to fill into preferred delivery vehicles such as gel capsules. Other problems currently associated with krill oil production include products with compromised purity, odor and taste; methods of obtaining low quality yields from raw materials; and products with lower than desired astaxanthin and phospholipid content. The inventors have unexpectedly discovered that impurities in krill oil produced by commercial extraction methods, rather than phospholipid content, cause viscosity-related problems. Specifically, removal of hexane-insoluble components such as rock salt from krill oil results in krill oil having reduced viscosity, improved handling properties, better stability, and improved organoleptic properties.

A related problem is that current methods for extracting lipids from krill are often very inefficient. In order to avoid extraction of contaminants that affect the quality of krill oil, the extraction efficiency of lipids is often sacrificed. Therefore, in order to extract high quality krill oil, current methods utilize gentle extraction techniques that leave large amounts of lipids in the starting krill material.

The present invention addresses these problems by first utilizing an efficient or high-yield process for the extraction of crude krill lipid compositions from krill starting materials such as krill meal. In some embodiments, the high yield extraction extracted about 70% to 90% w/w of the total available lipids in the krill biomass, compared to about 66% yield seen in previous extraction methods utilizing protic solvents . The crude krill lipid composition is then desalted to provide a desalted krill lipid composition containing about 30% to 50% w/w phospholipids. The desalinated krill lipid composition is suitable for use as nutritional supplements, dietary supplements and in functional foods. Desalted krill lipid compositions are also useful as superior materials for the production of krill phospholipid concentrates and neutral lipid concentrates containing high levels of astaxanthin. As described below, the present invention also provides a method for fractionating and separating krill phospholipid concentrates and krill neutral lipid concentrates by controlled fractionation of the desalted krill lipid composition with alcohol, followed by Cryocentrifugation was performed. The end result is a high quality krill lipid concentrate composition comprising about 50% and up to about 85% phospholipids w/w and a krill neutral lipid concentrate composition with high levels of astaxanthin. Astaxanthin can be further purified from the krill neutral lipid concentrate composition. The krill neutral lipid concentrate composition of purified astaxanthin can be blended with the krill phospholipid concentrate composition to provide a krill lipid composition with desired amounts of phospholipids and astaxanthin.

The combination of these method steps provides an efficient, flexible platform for producing high quality products from krill starting material. High quality products are typically characterized by low viscosity, little or no odor, improved taste, improved stability, low lysophospholipid content and low levels of unwanted materials or contaminants such as solvents, copper and other metal auxiliaries Oxidizing agents, total arsenic (including organic and inorganic arsenic), trimethylamine oxide and ethyl esters.

The remainder of the description is subdivided as follows: 1) starting material; 2) solvent extraction from krill meal; 3) desalting; 4) lipid and astaxanthin concentrations; 5) formulation of krill phospholipid composition; and 6 ) Use of krill phospholipid compositions.

1. Starting Materials

The present invention is not limited to the use of any particular biological starting material. The biological starting material may preferably be or be produced from algal biomass, plant biomass or marine animal biomass. In a preferred embodiment, marine animal biomass is utilized as starting material. Suitable marine animal biomass includes, but is not limited to, krill, crabs, Calanus, plankton, eggs, crayfish, shrimp, fish (especially herring), mollusks (including cephalopods such as squid) ), plants and algae. The biological starting material may be fresh or frozen, or may be material produced from algal, plant or marine animal biomass, such as meal, powder, hydrolysate or coagulum (paste). The paste can be a wet paste or a dry paste. In some preferred embodiments, the biological starting material is krill material, such as krill meal, krill hydrolysate, krill coagulum, or fresh or frozen krill. Any kind of krill can be used. In preferred embodiments, the krill is Antarctic krill or Pacific krill.

In some particularly preferred embodiments, the biological starting material is krill meal. Krill meal can preferably be made by any standard marine animal meal process. Typically, krill meal is produced by cooking freshly caught krill at low temperature (about 80°C-85°C) and drying to reduce the moisture content to about 5-8% and then grinding. In embodiments where the product is intended for human consumption, the powder is preferably packaged and stored under nitrogen without the addition of antioxidants.

Thus, the methods of the present invention can be used with a wide variety of starting materials. The rest of the discussion of the method generally refers to the use of krill meal as a starting material. It will be understood, however, that any of the starting materials contemplated herein can be substituted for krill meal in the process.

2. Solvent extraction from krill meal

In the first step of the extraction method, krill meal is mixed with a suitable solvent to extract lipids from the meal. In contrast to prior art methods, the present invention utilizes conditions that preferably extract the maximum amount of lipids from krill meal at the expense of increased amounts of contaminants in the initial solvent extract. In a preferred embodiment, the solvent is an organic protic solvent, however, other solvents known for extraction of food grade lipids, such as acetone, hexane, and the like, may also be used. Suitable organic protic solvents include, but are not limited to, n-butanol, n-propanol, isopropanol, nitromethane, ethanol, and methanol. In a particularly preferred embodiment, the protic solvent is ethanol.

In preferred embodiments, the concentration of protic solvent used in the initial solvent extraction step is at least 90%, preferably about 94% to 98%, more preferably about 95% to 97%, and most preferably about 96% % (eg, 96% ethanol or methanol).

In some embodiments, the protic solvent and biological starting material are in a ratio of about 1:1 to 10:1, preferably about 3:1 to 6:1, more preferably about 4:1 to 5, protic solvent:biostarting material : 1 and most preferably in a ratio of about 4.4: 1.

In preferred embodiments, the biological starting material uses a protic solvent at about 5°C to 65°C, about 20°C to about 60°C, preferably about 30°C to 50°C, more preferably about 30°C to 50°C and most preferably The extraction is preferably carried out at a temperature of about 40°C. In some embodiments, the extraction time (ie, the amount of time the biological starting material is contacted with the solvent) is about 10 minutes to about 2 hours, preferably about 15 minutes to 60 minutes, more preferably about 20 minutes to about 45 minutes And most preferably about 30 minutes.

After the extraction step, the crude krill lipid solution containing soluble lipids from krill meal is separated from the solvent/krill meal mixture, eg by decantation and or filtration. The insoluble material containing proteins and other useful materials is then dried to recover ethanol. The remainder of the protein-enriched powder product can then be used in food products, protein supplements, animal feed, and the like. In some embodiments, the decant solution containing soluble lipids has a dry matter content of about 4% to 9% w/w, preferably about 5.5% to 7.5% w/w and most preferably about 6% to 7% w/w % w/w, where w/w refers to dry matter weight as a percentage of total solution weight. In preferred embodiments, the dry matter consists essentially of crude krill lipids, and preferably has a lipid content of greater than 90%, 95%, 96%, 97%, 98% or 99% w/w, wherein w/w refers to lipid weight as a percentage of total dry matter weight.

The composition of crude krill lipids can preferably be characterized as follows. In some embodiments, the crude krill lipid preferably comprises from about 30% w/w to 50% w/w phospholipid, more preferably from about 35% w/w to about 45% w/w phospholipid, and most preferably About 40% w/w phospholipids, where w/w refers to phospholipid weight as a percentage of total crude krill lipid weight. In some embodiments, the crude krill lipid preferably comprises from about 26% w/w to 46% w/w triglycerides, more preferably from about 31% w/w to about 41% w/w triglycerides, And most preferably about 36% w/w triglycerides, where w/w refers to triglyceride weight as a percentage of total crude krill lipid weight. In some embodiments, the crude krill lipid preferably comprises from about 1% w/w to 7% w/w diglycerides, more preferably from about 1.5% w/w to about 4.5% w/w diglycerides, And most preferably about 3% w/w diglycerides, where w/w refers to the weight of the diglycerides as a percentage of the total crude krill lipid weight. In some embodiments, the crude krill lipid preferably comprises from about 2% w/w to 12% w/w free fatty acids, more preferably from about 4.5% w/w to about 9.5% w/w free fatty acids, and most preferably Preferably about 7% w/w free fatty acid, where w/w refers to free fatty acid weight as a percentage of total crude krill lipid weight. In some embodiments, the crude krill lipid preferably comprises about 1% w/w to 7% w/w cholesterol, more preferably about 1.5% w/w to about 4.5% w/w cholesterol, and most preferably About 3% w/w cholesterol, where w/w refers to cholesterol weight as a percentage of total crude krill lipid weight. In some embodiments, the crude krill lipid preferably comprises from about 0.1% w/w to 2% w/w cholesteryl ester, more preferably from about 0.2% w/w to about 1.0% w/w cholesteryl ester, and most preferably Preferably about 0.5% w/w cholesterol ester, where w/w refers to cholesterol ester weight as a percentage of total crude krill lipid weight. In some embodiments, the crude krill lipid preferably comprises about 0.5% w/w to 5% w/w inorganic salts, more preferably about 0.8% w/w to about 3.2% w/w inorganic salts, and most preferably Preferably about 1.2% to 2.8% w/w inorganic salt, where w/w refers to inorganic salt weight as a percentage of total crude krill lipid weight. In some embodiments, the crude krill lipid preferably comprises about 0.5% w/w to 5% w/w tertiary amines (eg trimethylamine oxide (TMAO) and other tertiary amines), more preferably about 0.8% w/w w to about 3.2% w/w tertiary amine, and most preferably about 1.2% to 2.8% w/w tertiary amine, where w/w refers to tertiary amine weight as a percentage of total crude krill lipid weight. In some embodiments, the tertiary amine is TMAO.

3. Desalination

In some embodiments, the crude krill lipid solution is desalted to remove hexane-insoluble materials such as insoluble inorganic salts (eg, NaCl and small or trace amounts of KCl and/or AlCl ₃ ) and unwanted compounds such as trimethylamine oxide, and metals such as copper and arsenic.

In some embodiments, the crude krill lipid solution is desalted by evaporating the solvent from the crude krill lipid solution to provide a crude krill lipid composition, and then subjecting the crude krill lipid composition to use Repeated washing with aqueous solvent. Suitable aqueous solvents include, but are not limited to, ethanol blended with water or deionized water such that the ethanol concentration is about 40% to 70%, preferably about 50% to 60%. In these embodiments, the crude krill lipid composition is mixed with a solvent, the lipid phase is recovered, and the aqueous phase is decanted. The washing steps can be repeated as desired, eg, 1, 2, 3, 4, 5 or more times. For each washing step, the ratio of aqueous solvent:crude krill lipid composition is preferably about 1:1 to 1:5, more preferably about 1:1 to 2.5:1, and most preferably about 1:1.7 .

In some embodiments, the crude lipid solution is desalted by chromatography. Suitable chromatography media include silica media, including but not including spherical silica and derivatized silicas such as C8 (octyl functionalized silica) and C18 (octadecyl functionalized silica) and ion exchange resins such as Dowex ^™ resins . In embodiments wherein chromatography is utilized, the crude krill lipid is preferably applied to the chromatography medium in a protic solvent, preferably the same solvent (eg, ethanol) used for the initial extraction. Standard column chromatography methods can be used, followed preferably by moving bed chromatography or simulated moving bed chromatography equipment.

In some embodiments, the krill oil extract comprising polar lipids, neutral lipids, trimethylamine oxide (TMAO), salts and astaxanthin is desalted by simulated moving bed chromatography. In some preferred embodiments, the krill extract is diluted in an effective amount of solvent to a concentration of between about 2% and about 7% by weight on a dry weight basis in the solvent to provide a desalination plant feed stream. In some embodiments, the solvent is preferably a mixture of ethanol and water having a ratio of ethanol to water of about 99:1 to about 95:5. In some embodiments, the desalination plant feed stream is introduced into at least one of a plurality of desalination stages in the krill oil simulated moving bed desalination zone, each desalination stage comprising a first desalination stage having a top and a bottom containing a cation exchange resin a column and a second column containing an anion exchange resin having a top and a bottom, the bottom of the first column is in fluid communication with the top of the second column, wherein at least a portion of the desalination stage is an active desalination stage, and at least one The desalination stations undergo desalination regeneration and a desalinated lipid-rich stream that is substantially free of TMAO and salts is drawn from one or more active desalination stations. In some embodiments, the solvent is preferably recovered from the desalted lipid-rich stream to provide desalted krill lipids. These methods are described in more detail in co-pending US Application No. 14/619,102, which is incorporated herein by reference in its entirety.

The dry matter composition of desalted krill lipids can preferably be characterized as follows. In some embodiments, desalted krill lipids preferably comprise from about 30% w/w to 50% w/w phospholipids, more preferably from about 35% w/w to about 45% w/w phospholipids, and most preferably 40% w/w phospholipids, where w/w refers to phospholipid weight as a percentage of total desalted krill lipid weight. In some embodiments, desalted krill lipids preferably comprise from about 32% w/w to 52% w/w triglycerides, more preferably from about 36% w/w to about 48% w/w triglycerides , and most preferably about 42% w/w triglycerides, where w/w refers to triglyceride weight as a percentage of total desalinated krill lipid weight. In some embodiments, the desalted krill lipids preferably comprise from about 3% w/w to 13% w/w free fatty acids, more preferably from about 5% w/w to about 11% w/w free fatty acids, and Most preferably about 8% w/w free fatty acid, where w/w refers to free fatty acid weight as a percentage of total desalted krill lipid weight. In some embodiments, the desalted krill lipid preferably comprises from about 0.5% w/w to 5% w/w lysophospholipid, more preferably from about 0.8% w/w to about 3.2% w/w lysophospholipid, and Most preferably about 1.2% to 2.8% w/w lysophospholipid, where w/w refers to lysophospholipid weight as a percentage of total desalted krill lipid weight. In some embodiments, desalinated krill lipids preferably contain less than about 1% w/w inorganic salts, more preferably less than about 0.5% w/w inorganic salts, even more preferably less than about 0.2% w inorganic salts /ww/w inorganic salt, and most preferably less than about 0.1% w/w inorganic salt, where w/w refers to inorganic salt weight as a percentage of total desalinated krill lipid weight. In some embodiments, the desalted krill lipid preferably contains less than about 5 mg N/100 g, more preferably less than about 3 mg N/100 g, even more preferably less than about 2 mg N/100 g, and most preferably Less than about 1 mg N/100 g, where the N content is used as a proxy for the trimethylamine oxide (TMAO) content. In some embodiments, the desalinated krill lipids contain less than about 10 ppm copper (Cu ⁺⁺ ), more preferably less than about 5 ppm Cu ⁺⁺ , even more preferably less than about 2 ppm Cu ⁺⁺ , and most preferably is less than about 1 ppm Cu ⁺⁺ . In some embodiments, the desalinated krill lipids contain less than about 10 ppm total arsenic (As ³⁺ , organic arsenic and inorganic arsenic), more preferably less than about 5 ppm total arsenic, even more preferably less than about 3 ppm total arsenic Arsenic, and most preferably less than about 1 ppm total arsenic. In some embodiments, the desalinated krill lipid preferably comprises about 0.01% to 2% w/w ethyl ester, more preferably about 0.01% to about 1.5% w/w ethyl ester, and most preferably about 0.01% to 1% w/w ethyl ester, where w/w refers to ethyl ester weight as a percentage of total desalted krill lipid weight. In some embodiments, the krill phospholipid concentrate preferably contains less than about 5%, 4%, 3%, or 2% w/w ethyl esters up to a lower limit of 0.01% ethyl esters (ie, between 5% and 0.01% w/w /w between ethyl ester, between 4% and 0.01% w/w ethyl ester, between 3% and 0.01% w/w ethyl ester, or between 2% and 0.01% w/w ethyl ester), more preferably less than about 1.5% w/w ethyl ester, and most preferably less than about 1% w/w ethyl ester, where w/w refers to the weight of ethyl ester as total desalted phosphorus Percentage of shrimp lipid weight. In some embodiments, the desalted krill lipids have a conductivity of less than about 50 μS/cm when measured using 5% dry matter in 95% ethanol, more preferably when measured using 5% dry matter in 95% ethanol has a conductivity of less than about 30 μS/cm when measured, and most preferably has a conductivity of less than about 20 μS/cm when measured using 5% dry matter in 95% ethanol. In some embodiments, the desalted krill lipids have a viscosity at 25°C of about 50 to 800 mPas, more preferably about 100 to 400 mPas at 25°C, and most preferably 180 to 400 mPas at 25°C 340mPas viscosity. In some embodiments, the desalted krill lipid composition has a pH of about 6.7 to 8.3 when measured in 95% ethanol.

4. Lipid and Astaxanthin Concentrations

In some embodiments, the present invention provides methods for concentrating lipids (eg, neutral lipids or polar lipids, such as phospholipids) and astaxanthin in solution. Although the method is described in terms of desalted krill lipids as described above, the method is generally applicable to any lipid fraction containing phospholipids.

Thus, in some embodiments, the dry matter content of the lipid composition containing phospholipids is adjusted to a predetermined level by adding or removing solvent and fractionating the result so that the phospholipids are predominantly partitioned into one phase and the neutral lipids partitioned into different phases. In some embodiments, a lipid composition containing phospholipids, such as desalted krill lipids, is mixed with a suitable protic solvent, preferably ethanol, such that the dry matter (ie, lipid) content of the resulting solution is about 10 % to 40% w/w, preferably about 15 to 35% w/w, more preferably about 18 to 30% w/w, and most preferably about 20 to 25% w/w. In embodiments where the desalting step has provided the lipids in a suitable protic alcohol solvent, such as where ethanol is used as the solvent for chromatography, the desalted krill lipid solution may preferably be evaporated to provide the desired dryness Substance content, i.e. about 10% to 40% w/w, preferably about 15% to 35% w/w, more preferably about 18% to 28% w/w, and most preferably about 20% to 22% w /w. Suitable methods for evaporation include, but are not limited to, evaporation under reduced pressure (eg, vacuum distillation), falling film evaporation, and solvent removal through membranes.

After adjusting the dry matter content to the desired level by adding or removing solvent, the solution is then fractionated into an upper light phase solution with enhanced phospholipid content and a lower heavy phase solution containing predominantly neutral lipids and high levels of astaxanthin . Preferably, the temperature of the solution is controlled during the fractionation step. In some embodiments, the temperature used for the fractionation step is about 0°C to about 20°C, preferably about 5°C to about 15°C, more preferably about 8°C to about 12°C, and most preferably about 10°C.

In some embodiments, the concentration of the protic solvent can be varied in order to control the phospholipid concentration in the lipid composition of the upper phase. In some embodiments, the protic solvent has a concentration of about 55% to 100%, more preferably about 65% to 98%. In some preferred embodiments, the protic solvent has a concentration of about 90% to 100%, more preferably about 92% to 98%, and most preferably about 95%. In these embodiments, the phospholipid content of the upper phase after fractionation is about 50% to 70% w/w, preferably about 55% to 65% w/w, and most preferably about 60%, based on lipid dry matter w/w. In still other preferred embodiments, the protic solvent has a concentration of about 80% to 90% w/w, more preferably about 82% to 88% w/w, and most preferably about 85% w/w. In these embodiments, the phospholipid content of the upper phase after fractionation is about 70% to 90% w/w, preferably about 75% to 85% w/w, and most preferably about 80%, based on lipid dry matter w/w.

In some embodiments, the upper and lower phases are separated by centrifugation, preferably cryogenic centrifugation using a two-phase or three-phase separator. In some embodiments, centrifugation is performed at about 0°C to about 30°C, more preferably about 0°C to about 10°C, and most preferably about 3°C to about 7°C. In general, the gravity utilized will depend on the ΔT between the phases. Low temperatures provide larger ΔT. In some preferred embodiments, the G force employed in the separation is from about 8000×G to about 15000×G.

In some embodiments, the method step of adjusting the dry matter content as described above by the centrifugation step is repeated one or more times.

In some embodiments, the upper light phase is collected and further processed. The solvent is preferably removed from the upper phase by one or more evaporation steps to obtain a krill phospholipid concentrate. The krill phospholipid concentrate preferably comprises from about 50% to 85% w/w phospholipid, and more preferably from about 55% to about 80% w/w phospholipid, wherein w/w refers to the weight of the phospholipid as a percentage of the total concentrate weight .

In some embodiments, the lower heavy phase is collected and further processed. In some embodiments, the solvent is removed from the lower phase to provide a krill neutral lipid concentrate. In some embodiments, the lower phase may be fractionated using a protic solvent and subjected to a second centrifugation step to recover additional phospholipids not recovered in the first fractionation step. Additionally, solvent is removed from the resulting lower phase to provide a krill neutral lipid concentrate. In both cases the krill neutral lipid concentrates were characterized by high levels of astaxanthin. In some embodiments, the krill neutral lipid concentrate can be combined or blended with the krill phospholipid concentrate to provide a lipid composition with desired levels of phospholipids, neutral lipids, and astaxanthin. In some embodiments, the krill neutral lipid concentrate can be further processed (eg, by chromatography) to provide an astaxanthin concentrate. The astaxanthin concentrate can then be combined or blended with the krill phospholipid concentrate to provide a lipid composition with desired levels of phospholipids and astaxanthin.

In some embodiments, the method further comprises the step of adding a triglyceride oil, such as a medium chain triglyceride oil or a long chain triglyceride oil, at any stage during the method. For example, triglyceride oil can be added to the collected light phase, heavy phase, phospholipid concentrate or neutral lipid concentrate. In some embodiments, the method steps of adjusting the dry matter content as described above by the centrifugation step and/or the evaporation step are repeated one or more times.

In some embodiments, krill phospholipids and neutral lipid concentrates are produced by additional chromatography steps. In these embodiments, at least a portion of the desalted lipid-rich stream described above is introduced into a polar liquid extraction zone comprising a fixed bed adsorber containing large molecules effective for adsorbing neutral lipids Porous styrene polymer bead type resin. In a preferred embodiment, the fixed bed chromatography step provides a polar lipid extraction stream comprising solvent and at least 50 wt % polar lipid by dry weight. In some preferred embodiments, the fixed bed adsorber is intermittently regenerated using a stream of hot ethanol at a thermal regeneration temperature between about 40°C and about 60°C to provide a stream comprising solvent, neutral lipid and astaxanthin of neutral lipid raffinate. In some embodiments, solvent is recovered from the polar lipid extract stream to provide a krill phospholipid concentrate and from the neutral lipid raffinate stream to provide a neutral lipid concentrate. These methods are described in more detail in co-pending US Application No. 14/619,102, which is incorporated herein by reference in its entirety.

In some embodiments, the krill phospholipid concentrate preferably comprises from about 5% w/w to 35% w/w triglycerides on a dry matter basis, more preferably from about 10% w/w to about 30% w/w Triglycerides, and most preferably about 15% to 25% w/w triglycerides, where w/w refers to triglyceride weight as a percentage of total krill phospholipid concentrate weight. In some embodiments, the krill phospholipid concentrate preferably comprises from about 2% w/w to 13% w/w free fatty acids, more preferably from about 4% w/w to about 11% w/w free fatty acids, and most preferably Preferably about 4% to 10% w/w free fatty acid, where w/w refers to free fatty acid weight as a percentage of total krill phospholipid concentrate weight. In some embodiments, the krill phospholipid concentrate preferably comprises about 0.5% w/w to 10% w/w lysophospholipid, more preferably about 0.8% w/w to about 7.0% w/w lysophospholipid, and most preferably about 0.8% w/w to about 7.0% w/w lysophospholipid Preferably less than about 5.0% w/w or 3.0% w/w lysophospholipid, where w/w refers to lysophospholipid weight as a percentage of total krill phospholipid concentrate weight. In some embodiments, the krill phospholipid concentrate preferably contains less than about 1% w/w inorganic salts, more preferably less than about 0.5% w/w inorganic salts, even more preferably less than about 0.2% w/w inorganic salts w inorganic salts, and most preferably less than about 0.1% w/w or 0.05% w/w inorganic salts, where w/w refers to inorganic salt weight as a percentage of total krill phospholipid concentrate weight. In some embodiments, the krill phospholipid concentrate preferably contains less than about 5 mg N/100 g, more preferably less than about 3 mg N/100 g, even more preferably less than about 2 mg N/100 g, and most preferably less At about 1 mgN/100 g, where the N content is used as a convenient proxy for the trimethylamine oxide (TMAO) content. In some embodiments, the krill phospholipid concentrate contains less than about 10 ppm copper (Cu ⁺⁺ ), more preferably less than about 5 ppm Cu ⁺⁺ , even more preferably less than about 2 ppm Cu ⁺⁺ , and most preferably Less than about 1 ppm Cu ⁺⁺ . In some embodiments, the krill phospholipid concentrate contains less than about 10 ppm total arsenic (As ³⁺ ), more preferably less than about 5 ppm total arsenic, even more preferably less than about 3 ppm total arsenic, and most preferably less At about 1 ppm total arsenic. In some embodiments, the krill phospholipid concentrate preferably comprises from about 0.01% to 2% w/w ethyl ester, more preferably from about 0.01% to about 1.5% w/w ethyl ester, and most preferably from about 0.01% to 1% w/w ethyl ester, where w/w refers to ethyl ester weight as a percentage of total krill phospholipid concentrate weight. In some embodiments, the krill phospholipid concentrate preferably comprises less than about 5%, 4%, 3% or 2% w/w ethyl esters up to a lower limit of 0.01% ethyl esters (ie, between 5% and 0.01% w/w /w between ethyl ester, between 4% and 0.01% w/w ethyl ester, between 3% and 0.01% w/w ethyl ester or between 2% and 0.01% w/w ethyl ester), more preferably less than about 1.5% w/w ethyl ester, and most preferably less than about 1% w/w ethyl ester, where w/w refers to the weight of ethyl ester as total krill phospholipids percent by weight of concentrate. In some embodiments, the krill phospholipid concentrate has a conductivity of less than about 50 μS/cm when measured using 5% dry matter in 95% ethanol, more preferably when measured using 5% dry matter in 95% ethanol Have a conductivity of less than about 30 μS/cm, and most preferably have a conductivity of less than about 20 μS/cm, 10 μS/cm, 5 μS/cm or 1 μS/cm when measured using 5% dry matter in 95% ethanol. In some embodiments, the krill phospholipid concentrate has a viscosity of about 400 to 2000 mPas at 35°C, more preferably about 500 to 1800 mPas at 35°C, and most preferably about 600 to 1800 mPas at 35°C 1600mPas viscosity. In some embodiments, the krill phospholipid concentrate has a pH of about 6.7 to 8.3 when measured in 95% ethanol.

In some embodiments, the krill neutral lipid concentrate preferably comprises from about 70% w/w to 95% w/w triglycerides on a dry matter basis, more preferably from about 75% w/w to about 95% w/w triglycerides, and most preferably about 88% to 92% w/w triglycerides, where w/w refers to triglyceride weight as a percentage of total krill neutral lipid concentrate weight. In some embodiments, the krill neutral lipid concentrate preferably comprises about 2% w/w to 20% w/w phospholipids, more preferably about 4% w/w to about 15% w/w phospholipids, and Most preferably about 5% to 10% w/w phospholipids, where w/w refers to the weight of the phospholipids as a percentage of the total krill neutral lipid concentrate weight.

In some embodiments, the krill neutral lipid concentrate preferably comprises about 0.5% w/w to 10% w/w free fatty acid, more preferably about 1% w/w to about 8% w/w free fatty acid , and most preferably about 1% to 5% w/w free fatty acid, where w/w refers to free fatty acid weight as a percentage of total krill neutral lipid concentrate weight. In some embodiments, the krill neutral lipid concentrate preferably comprises from about 0.1% w/w to 2% w/w lysophospholipid, more preferably from about 0.2% w/w to about 1.0% w/w lysophospholipid , and most preferably less than about 0.5% w/w or 0.2% w/w lysophospholipid, where w/w refers to lysophospholipid weight as a percentage of total krill neutral lipid concentrate weight. In some embodiments, the krill neutral lipid concentrate preferably contains less than about 1% w/w inorganic salt, more preferably less than about 0.5% w/w inorganic salt, even more preferably less than about 0.2 % w/w inorganic salt, and most preferably less than about 0.1% w/w or 0.05% w/w inorganic salt, where w/w refers to inorganic salt weight as a percentage of total krill neutral lipid concentrate weight . In some embodiments, the krill neutral lipid concentrate preferably contains less than about 5 mg N/100 g, more preferably less than about 3 mg N/100 g, even more preferably less than about 2 mg N/100 g, and most preferably is less than about 1 mg N/100 g, where the N content is used as a convenient proxy for the trimethylamine oxide (TMAO) content. In some embodiments, the krill neutral lipid concentrate contains less than about 10 ppm copper (Cu ⁺⁺ ), more preferably less than about 5 ppm Cu ⁺⁺ , even more preferably less than about 2 ppm Cu ⁺⁺ , and Most preferably less than about 1 ppm Cu ⁺⁺ . In some embodiments, the krill neutral lipid concentrate contains less than about 10 ppm total arsenic (As ³⁺ ), more preferably less than about 5 ppm total arsenic, even more preferably less than about 3 ppm total arsenic, and most preferably less than about 3 ppm total arsenic Preferably less than about 1 ppm total arsenic. In some embodiments, the krill neutral lipid concentrate preferably comprises about 0.01% to 2% w/w ethyl ester, more preferably about 0.01% to about 1.5% w/w ethyl ester, and most preferably about 0.01% to 1% w/w ethyl ester, where w/w refers to ethyl ester weight as a percentage of total krill neutral lipid concentrate weight. In some embodiments, the krill neutral lipid concentrate preferably contains less than about 2% w/w ethyl ester, more preferably less than about 1.5% w/w ethyl ester, and most preferably less than about 1 % w/w ethyl ester, where w/w refers to ethyl ester weight as a percentage of total krill neutral lipid concentrate weight. In some embodiments, the krill neutral lipid concentrate has a conductivity of less than about 50 μS/cm when measured using 5% dry matter in 95% ethanol, more preferably when using 5% dry matter in 95% ethanol The substance has a conductivity less than about 30 μS/cm when measured, and most preferably less than about 20 μS/cm, 10 μS/cm, 5 μS/cm or 1 μS/cm when measured using 5% dry matter in 95% ethanol Rate. In some embodiments, the krill neutral lipid concentrate has a viscosity of less than about 400 mPas at 25°C, more preferably a viscosity of less than about 300 mPas at 25°C, and most preferably a viscosity of less than about 300 mPas at 25°C Viscosity of less than about 200 mPas. In some embodiments, the krill neutral lipid concentrate has a pH of about 7.0 to 9.0 when measured in 95% ethanol.

In some embodiments, the neutral lipid concentrate may preferably be further processed to provide an astaxanthin ester concentrate. In some embodiments, the astaxanthin ester concentrate is produced by introducing all or at least a portion of the neutral lipid raffinate stream to the astaxanthin extraction zone and contacting the stream activated carbon adsorbent therein to adsorb the astaxanthin and providing a neutral lipid-enriched stream comprising solvent and neutral lipids; and regenerating the stream activated carbon with anisole to desorb astaxanthin, thereby providing anisole- and astaxanthin-enriched shrimp The flow of cyanine. In some embodiments, the anisole is preferably recovered from the astaxanthin-rich stream to provide an astaxanthin ester concentrate. These methods are described in more detail in co-pending US Application No. 14/619,102, which is incorporated herein by reference in its entirety. In some preferred embodiments, the astaxanthin ester concentrate comprises about 300 or 400 ppm to about 4000 ppm astaxanthin ester, more preferably about 400 to about 3000 ppm astaxanthin ester and most preferably greater than about 500 ppm astaxanthin ester . In further preferred embodiments, the astaxanthin ester concentrate comprises greater than about 95%, 96%, 97%, 98% or 99% w/w krill neutral lipids, wherein w/w refers to neutral Krill lipid weight as a percentage of total astaxanthin ester concentrate weight.

5. Formulation of Krill Phospholipid Composition

The krill phospholipid composition of the present invention is preferably administered orally. Thus, in some embodiments, compositions of the present invention, such as those described in the preceding sections, are included in acceptable excipients and/or carriers for oral consumption. The actual form of the carrier, and therefore its composition, is not critical. The carrier can be a liquid, gel, caplet, capsule, powder, solid tablet (coated or uncoated), tea, and the like. The composition is preferably in the form of a tablet or capsule and most preferably in the form of a soft gel capsule. Suitable excipients and/or carriers include vegetable oils, fish oil, krill oil, maltodextrin, calcium carbonate, dicalcium phosphate, tricalcium phosphate, microcrystalline cellulose, dextrose, rice flour, magnesium stearate, Stearic acid, croscarmellose sodium, sodium starch glycolate, crospovidone, sucrose, vegetable gum, lactose, methylcellulose, povidone, carboxymethylcellulose, corn starch, etc. ( including mixtures thereof). Preferred carriers include calcium carbonate, magnesium stearate, maltodextrin and mixtures thereof. The various ingredients and excipients and/or carriers are mixed and formed into the desired form using conventional techniques. The tablets or capsules of the present invention may be coated with an enteric coating that dissolves at a pH of about 6.0 to 7.0. A suitable enteric coating that dissolves in the small intestine but not in the stomach is cellulose acetate phthalate. Additional details regarding techniques for formulation and administration can be found in the latest edition of Remington's Pharmaceutical Sciences (Maack Publishing Co., Easton, PA). For intravenous or oral administration, the omega-3 compounds and compositions of the present invention may preferably be provided as an emulsion.

In some embodiments, the krill phospholipid composition is formulated for oral administration with a flavoring or sweetening agent. Examples of suitable flavoring agents include, but are not limited to, pure fennel extract, artificial banana extract, artificial cherry extract, chocolate extract, pure lemon extract, pure orange extract, pure peppermint extract, artificial pineapple extract, artificial Rum extract, artificial strawberry extract, or pure vanilla extract; or volatile oils such as melissa oil, bay oil, bergamot oil, cedar oil, walnut oil, cherry oil, cinnamon oil, clove oil, or peppermint oil ; peanut butter, chocolate spice, vanilla crumbs, butterscotch or toffee. In one embodiment, the dietary supplement contains cocoa powder or chocolate. Emulsifiers can be added to stabilize the final product. Examples of suitable emulsifiers include, but are not limited to, lecithin (eg, from egg or soy) and/or mono- and diglycerides. Other emulsifiers will be apparent to the skilled person and the selection of suitable emulsifiers will depend in part on the formulation and the final product. In addition to the carbohydrates described above, nutritional supplements may contain natural or artificial (preferably low calorie) sweeteners such as sugars, cyclamate, aspartamine, aspartame Partame, acesulfame potassium and/or sorbitol.

The krill phospholipid compositions of the present invention can also be delivered as dietary supplements, nutritional supplements or functional foods.

Dietary supplements may contain one or more inert ingredients, especially where it is desired to limit the number of calories added to the diet through dietary supplements. For example, dietary supplements of the present invention may also contain optional ingredients including, for example, herbs, vitamins, minerals, enhancers, colorants, sweeteners, flavoring agents, inert ingredients, and the like. For example, dietary supplements of the present invention may contain one or more of the following: ascorbates (ascorbic acid, mineral ascorbic acid, rose hips, amphora, etc.), dehydroepiandrosterone (DHEA), green tea (polyphenols), Inositol, Kelp, Haematoderma Palmitate, Bioflavonoids, Maltodextrin, Nettle, Niacin, Niacinamide, Rosemary, Selenium, Silica (Silica, Silica, Vitex, Horsetail, etc.), Spirulina, zinc, etc. Such optional ingredients may be in naturally occurring or concentrated form.

In some embodiments, the dietary supplement further comprises vitamins and minerals, including but not limited to tribasic calcium phosphate or calcium acetate; dipotassium hydrogen phosphate; magnesium sulfate or oxide; salt (sodium chloride); potassium chloride or Potassium acetate; ascorbic acid; iron orthophosphate; nicotinamide; zinc sulfate or zinc oxide; calcium pantothenate; copper gluconate; riboflavin; beta-carotene; pyridoxine hydrochloride; thiamine mononitrate; folic acid; biotin ; chromium chloride or chromium picolonate; potassium iodide; sodium selenate; sodium molybdate; phylloquinone; vitamin D ₃ ; cyanocobalamin; sodium selenite; copper sulfate; vitamin A; vitamin C; muscle Alcohol; Potassium Iodide. Suitable dosages of vitamins and minerals can be obtained, for example, by consulting the US RDA guidelines.

In other embodiments, the present invention provides nutritional supplements (eg, energy bars or meal replacement bars or beverages) comprising the krill phospholipid compositions of the present invention. In a preferred embodiment, the nutritional supplement comprises an effective amount of a component as described above. Nutritional supplements can be used as meal or snack replacements and generally provide nutritional calories. Preferably, the nutritional supplement provides balanced amounts of carbohydrates, protein and fat. The nutritional supplement may also contain carbohydrates, monosaccharides, medium chain length sugars or polysaccharides, or combinations thereof. Monosaccharides can be selected for the desired organoleptic properties. Uncooked cornstarch is an example of a complex carbohydrate. If it is desired that the cornstarch should maintain its high molecular weight structure, it should only be included in uncooked or heat-treated food preparations or parts thereof, as heat will break down complex carbohydrates into simple carbohydrates, where simple carbohydrates are Monosaccharides or disaccharides. In one embodiment, the nutritional supplement contains a combination of carbohydrate sources at three chain length levels (monosaccharides, medium chain and complex sugars; eg, sucrose, maltodextrin, and uncooked cornstarch).

In still other embodiments, the present invention provides food products, prepared food products or foodstuffs (ie, functional foods) comprising the krill phospholipid compositions of the present invention. In a preferred embodiment, the food product comprises an effective amount of a component as described above. For example, in some embodiments, beverages and solid or semi-solid foods comprising fatty acids or derivatives thereof are provided. These forms include, but are not limited to, beverages (eg, soft drinks, milk and other milk-based beverages, and dietary beverages), baked goods, puddings, dairy products, candies, snacks, or frozen confections or novelties (eg, ice cream, shakes), prepared Frozen meals, confectionery, fast food products (such as chips), soups, spreads, sauces, salad dressings, prepared meat products, cheese, yogurt and any other fatty or oily food and food ingredients (such as flour).

In some preferred embodiments, the krill phospholipid composition is incorporated into a chewable base. Preferred chewable bases are gummies and gelatin-based gummies. Exemplary gummies include gummi bears, gummi worms, gummi frogs, gummi hamburgers, gummi cherries, soda bottle gummies ( gummi sodabottles, gummi sharks, gummi army men, gummi hippopotami, gummi lobsters, gummi watermelons, gummi octopus octopuses), gummi apples, gummi peaches, and gummi oranges. The terms "gummi" and "gummy" are used interchangeably herein.

In some particularly preferred embodiments, the chewable base material is a sweetening material commonly referred to as gummy or jelly material. Gummies or jelly candies are a broad general type of gelatin-based chewy candy. Gummy Bears are the most popular and well-known gummy candies. Other shapes are also available and gummy candies are sometimes combined with other forms of candy such as marshmallows and chocolate and are also made sour.

In a preferred embodiment, the chewable matrix material comprises a gelling agent, which may be any physiologically tolerated gelling agent (preferably a sugar (eg oligo- or polysaccharide), protein or glycoprotein) or capable of forming soft Combination of a textured, chewable, self-supporting chewable gel. Many such materials are known in the food and pharmaceutical industries and discussed in eg Handbook of hydrocolloids, G O Phillips and P A Williams (eds), Woodhead Publishing, Cambridge, UK, 2000. The gelling agent is preferably a material capable of sol-gel transformation eg under the influence of changes in physiological parameters such as temperature, pH, presence of metal ions (eg Group 1 or 2 metal ions) and the like. Preferred gelling agents include gelatin, alginate and carrageenan. However, the use of gelling agents is particularly preferred because it ensures disintegration in the throat of the captured fragments and because cores with the desired properties can be easily produced using gelatin.

The gelatin used as the gelling agent in the chewable matrix of the present invention can be produced from any mammalian collagen or from any aquatic organism, however, it is preferred to use gelatin from saltwater fish and in particular cold and warm water fish. Preference is given to gelatins having an amino acid content of 5% to 25% by weight, more precisely those gelatins having an amino acid content of 10% to 25% by weight. The gelatin will generally have a weight average molecular weight in the range of 10 to 250 kDa, preferably 75 to 220 kDa, especially 80 to 200 kDa. Gelatin with no Bloom value or with a low Bloom value of 60-300, 150-300 and especially 90-200 is preferred. Where a Bloom-free gelatin is used, such as cold water fish gelatin, this will typically be used with another gelatin or other gelling agent. A combination of cold water fish gelatin and warm water fish gelatin is particularly preferred. Gelatin will generally be present in the aqueous phase at a concentration of 1% to 50% by weight, preferably 2% to 35% by weight, especially 5% to 25% by weight. In the case of a mixture of gelatin and polysaccharide, the weight ratio of gelatin to polysaccharide in the aqueous phase will generally be 50:1 to 5:1, preferably 40:1 to 9:1, especially 20:1 to 10:1 .

In the case of using polysaccharides or mixtures of polysaccharides and gelatin as gelling agent, preference is given to using natural polysaccharides, synthetic polysaccharides or semi-synthetic polysaccharides, such as polysaccharides from plants, fish, terrestrial mammals, algae, bacteria and derivatives thereof and Fragmented product. Typical marine polysaccharides include carrageenan, alginate, agar and chitosan.

Typical plant polysaccharides include pectin. Typical microbial polysaccharides include gellan gum and scleroglucan. Charged, eg electrostatically charged and/or sulfated polysaccharides are preferably used, as is the use of marine polysaccharides, in particular carrageenan and alginates, especially carrageenan. The carrageenan family (including iota-carrageenan and kappa-carrageenan) is a family of linear sulfated polysaccharides produced by red algae. The repeating disaccharide units in kappa-carrageenan are β-D-galactose-4-sulfate and 3,6-anhydride-α-D-galactose, while the repeating disaccharide units in iota-carrageenan The sugar units are β-D-galactose-4-sulfate and 3,6-anhydride-α-D-galactose-2-sulfate. Both kappa-carrageenan and iota-carrageenan are used in food preparation. Carrageenan is used as a stabilizer, emulsifier, gelling agent and fat replacer.

Both iota carrageenans and kappa carrageenans form salt-cured or cold-cured reversible gels in aqueous environments. Coiled-coil transitions and aggregation of helices form a gel network. Kappa-carrageenan has binding sites for specific monovalent cations, resulting in gel formation with reduced shear and elastic modulus in the order Cs ⁺ >K ⁺ >>Na ⁺ >Li ⁺ . Generally, increasing salt concentration enhances the elastic modulus and curing and melting temperatures of kappa-carrageenan. When using kappa-carrageenan according to the invention, for example in a concentration of 100 mM, more precisely 50 mM, it is preferred to use a water-soluble potassium, rubidium or cesium compound, in particular a potassium compound and in particular a naturally occurring compound ( such as salt). Salt-dependent conformational transitions are also seen for iota-carrageenan. The molecule is also known to undergo coiled-coil transition and strong helical stability in the presence of multivalent cations such as Ca ²⁺ . When iota-carrageenan is used according to the invention, for example in concentrations of up to 100 mM, it is preferred to use water-soluble calcium, strontium, barium, iron or aluminium compounds, especially calcium compounds and in particular naturally occurring compounds such as salts ).

The polysaccharide gelling agent used according to the present invention will generally have a weight average molecular weight of 5 kDa to 2 MDa, preferably 10 kDa to 1 MDa, most preferably 100 kDa to 900 kDa, in particular 200 to 800 kDa. The gelling agent will generally be used in a concentration of 0.01 to 5 wt%, preferably 0.1 to 1.5 wt%, in particular 0.2 to 1 wt% in the aqueous phase. Where monovalent or multivalent cations (usually Group 1 or Group 2 metal ions) are included in the aqueous phase, this is typically at a concentration in the range 2.5 to 100 mM, specifically 5 to 50 mM.

In addition to gelling agents and water and any desired gelation initiators, other physiologically tolerated materials may be present in the chewable base, such as emulsifiers, emulsion stabilizers, pH adjusters, viscosity adjusters, sweeteners , fillers, vitamins (eg vitamin C, thiamin, riboflavin, niacin, vitamin B6, vitamin B12, folic acid, pantothenic acid), minerals, fragrances, seasonings, making agents, pigments, physiological activity agents, etc., as described in detail above with respect to additional materials that may be included in the oxidizable fatty acid composition.

The chewable base has a gelling temperature in the range of preferably 10C to 30C, more preferably 15C to 28C, and a melting temperature in the range of 20C to 80C, more preferably 24C to 60C, exactly 28C to 50C.

Where a sweetener is included in the chewable base, this will typically be selected from natural sweeteners such as sucrose, fructose, glucose, reducing glucose, maltose, xylitol, maltitol, sorbitol, mannitol, lactitol , isomalt, erythritol, polyglycols, polyglucitol, glycerin, stevia, agave syrup, invertisyrup, and artificial sweeteners such as aspartame, acesulfame Potassium acid, neotame, saccharin, sucralose. Preference is given to using non-cariogenic sweeteners and particularly preferably using xylitol. Preferred flavors include orange, raspberry, cherry, lemon, blood orange, grapefruit, strawberry, blueberry, blackberry, and combinations thereof, especially orange and raspberry.

Mass production of fondant candies (eg, gummy bears) involves mixing the fondant candy ingredients and pouring the resulting mixture into a number of starch-lined (eg, cornstarch-lined) pans/molds. The cornstarch prevents the gummy bears from sticking to the molds and allows the gummies to release easily once set. First, create the desired feature mold and repeat with the machine as needed. Optionally, starch powder is applied to the feature mold. The fondant confectionery ingredients such as sugar, glucose syrup, gelatin and water are mixed together and heated. In one aspect, the ingredients are mixed with pigments and flavors that impart the bear's signature look and taste. The melted gelatin mixture is poured into molds and allowed to cool and set before packaging or consumption. Preferably, the fondant candy is then heated and placed in a large drum to apply the isolated Bacillus coagulans and sweetener (eg sugar).

In some preferred embodiments, the production of fudge confectionery includes the following steps. Colloid batches and puree batches are formed and combined with corn syrup and sugar to form a syrup base. The colloid batch contains an aqueous solution of the gelling agent at a level of 5 wt% to 15 wt% gelling agent, more preferably 7 wt% to 12 wt%, based on the total weight of the colloid batch. Keep the colloid batch at a temperature of 170 to 190F. The puree batch preferably contains water, fruit puree and/or high fructose corn syrup or other sweetener, thin starch and sodium citrate. Keep it at 65 to 75F. Preferably, the puree has a Brix of 10 to 45, more preferably 25 to 40. Preferably, the puree batch contains multiple fruit purees. Fruit purees include typical fruit purees, juices or fruit powders. The puree batch contains 30-40 wt% water, 0-40 wt% fruit puree, 0-40 wt% high fructose corn syrup, 25-35 wt% thin starch and 0.0% to 2.0% by weight of sodium citrate. In a mixing tank, combine 25-40 wt% additional corn syrup with 15-40 wt% caster sugar, 10-15 wt% colloid batch, and 20-30 wt% fruit Puree batches are combined to form a syrup base. Preferably, the corn syrup is about 42DE corn syrup, however, as one of ordinary skill in the art will appreciate, other DE corn syrups may be used. The base syrup components are thoroughly mixed in the holding tank and maintained at 130 to 150F.

The syrup base is then cooked to a Brix of 70 to 85 Brix, more preferably 75 to 80 Brix. In one embodiment, the syrup base is passed through a coil cooker and heated to a temperature of 250 to 325F to cook it. Other cooking methods can be used, as will be understood by those of ordinary skill in the art. The cooked syrup base is preferably subjected to vacuum to further increase the Brix to the desired range. Keep the cooked syrup base at about 200F until use. The acidulant solution is preferably added to the cooked base syrup along with color and flavor just prior to deposition in the starch mold. In one aspect, the acidulant solution comprises ascorbic acid in an amount from 15% to 20% by weight, citric acid in an amount from 10% to 20% by weight, and apple in an amount from 5% to 10% by weight acid, and the rest contains water. As will be understood by one of ordinary skill in the art, other edible acids may be used in place of or in addition to those listed. In one aspect, 95% to 97% by weight of the cooked base syrup is combined with 2% to 3% by weight of the acidulant solution and the remainder comprises flavors and colors. Optionally, an acidulant solution is used to bring the pH of the base syrup to 2.6 to 3.2. One of ordinary skill in the art would have no difficulty in selecting suitable pigments and flavors. The combined mixture is then deposited into starch molds, eg, using a Mogul starch molder. Such starch molding machines are well known to those of ordinary skill in the art. In one aspect, 0.3 to 3 grams of base syrup is deposited into each mold cavity. In some preferred embodiments, a starch molding machine ("Mogul") for forming gummy bears includes two nozzles for each mold and a device for delivering small soft gel capsules. The first nozzle provides about 40% of the mold volume before one capsule is placed in the mold. Finally, the second nozzle fills the mold. Then quickly cook the gummy bears containing the capsules. The starch tray with the deposited base syrup was transferred to a drying chamber where it was held for 12 to 48 hours. Optionally, the pan is first held at a temperature of 130 to 150F for 10 to 15 hours, and then cooled to 70 to 80F and held at that temperature for 6 to 12 hours. The gelatinized starch molded food pieces are then removed from the pan, allowing the starch to be recycled.

In some embodiments of the present invention, it is contemplated that the oil within the capsule is protected from hydrolysis by water present in the product. Gummies and other jelly candies contain not too high amounts of water and additionally, the acidity is low enough to counteract bacterial growth.

In some embodiments, the present invention provides compositions comprising the krill phospholipid composition described above and one or more additional omega-3 fatty acid derivatives or free fatty acids. Omega-3 fatty acid derivatives or free fatty acids can be derived from a neutral lipid extract or another source such as fish oil or an omega-3 ester concentrate. In some embodiments, the one or more additional omega-3 fatty acid derivatives are selected from omega-3 esters and glycerides. For example, in some embodiments, the composition may comprise from about 1% to about 60% w/w krill oil composition (ie, phospholipid compound weight/total composition weight), with the remaining 99% to 40% w/w The composition is an omega-3 glyceride, ester, or free fatty acid, or a combination thereof (ie, weight of omega-3 glyceride, ester, or free fatty acid, or a combination thereof/total weight of the composition). In some embodiments, the composition may comprise from about 5% to about 60% w/w phospholipids, with the remaining 95% to 40% w/w of the composition being omega-3 glycerides, esters, or free fatty acids, or combinations thereof. In some embodiments, the composition may comprise from about 20% to about 60% w/w phospholipids, with the remaining 80% to 40% w/w of the composition being omega-3 glycerides, esters, or free fatty acids, or combinations thereof. In some embodiments, the composition may comprise from about 30% to about 60% w/w phospholipids, with the remaining 70% to 40% w/w of the composition being omega-3 glycerides, esters, or free fatty acids, or combinations thereof. In some embodiments, the composition may comprise from about 40% to about 60% w/w phospholipids, with the remaining 60% to 40% w/w of the composition being omega-3 glycerides, esters, or free fatty acids, or combinations thereof. In some embodiments, the composition may comprise from about 50% to about 60% w/w phospholipids, with the remaining 50% to 40% w/w of the composition being omega-3 glycerides, esters, or free fatty acids, or combinations thereof.

6. Use of krill phospholipid composition

In some embodiments, a compound or composition as described above is administered to a subject in need thereof to treat a disease or condition associated with red blood cells and cell membranes, and in particular an abnormality in red blood cells or cell membranes disease or condition. In some embodiments, the condition or disease is sickle cell disease, sickle cell anemia, or sickle cell trait. In some embodiments, the condition or disease is thalassemia (alpha, beta, or delta), thalassemia with hemoglobinopathies (hemoglobin E, hemoglobin S, or hemoglobin C), splenomegaly, or membrane abnormalities such as acanthocytes or spinous/spike cells, codocytes (target cells), spinous cells (spicy cells), oval and oval cells, spherocytes, cleft cells (mouth cells), and degmacytes (“ bite cells").

In some embodiments, an effective amount of a compound or composition described above is administered to a subject in need thereof to treat or prevent a cardiovascular disorder or metabolic syndrome. In some embodiments, the cardiovascular disorder is selected from the group consisting of atherosclerosis, arteriosclerosis, coronary heart (carotid) disease (CHD or CAD), acute coronary syndrome (or ACS), valvular heart disease, aorta, and two Cubic valve disorders, arrhythmia/atrial fibrillation, cardiomyopathy and heart failure, angina pectoris, acute myocardial infarction (or AMI), hypertension, orthostatic hypotension, shock, embolism (pulmonary and venous), endocardium Inflammation, diseases of arteries, aorta and their branches, disorders of the peripheral vascular system (peripheral arterial disease or PAD), Kawasaki disease, congenital heart disease (cardiovascular defects) and stroke (cerebrovascular disease), dyslipidemia , Hypertriglyceridemia, hypertension, heart failure, cardiac arrhythmia, low HDL level, high LDL level, stable angina, coronary heart disease, acute myocardial infarction, secondary prevention of myocardial infarction, cardiomyopathy, endocardium Inflammation, type 2 diabetes, insulin resistance, impaired glucose tolerance, hypercholesterolemia, stroke, hyperlipidemia, hyperlipoproteinemia, chronic kidney disease, intermittent claudication, hyperphosphatemia, omega-3 deficiency disease, phospholipid deficiency, carotid atherosclerosis, peripheral arterial disease, diabetic nephropathy, hypercholesterolemia in HIV infection, acute coronary syndrome (ACS), nonalcoholic fatty liver/nonalcoholic steatohepatitis (NAFLD/NASH), arterial occlusive disease, cerebral atherosclerosis, arteriosclerosis, cerebrovascular disorders, myocardial ischemia, coagulopathy leading to thrombosis in blood vessels, and diabetic autonomic neuropathy.

In some embodiments, an effective amount of a compound or composition described above is administered to a subject in need thereof to treat, prevent or ameliorate cognition and/or cognitive disease, disorder or impairment (memory, attention concentration, learning (deficits)) or the treatment or prevention of neurodegenerative disorders. In some embodiments, the cognitive disease, disorder or impairment is selected from attention deficit disorder (ADD), attention deficit hyperactivity disorder (ADHD), autism/autism-like disorder (ASD), (dyslexia, age-related memory) Impairment and learning disabilities, amnesia, mild cognitive impairment, cognitively impaired non-dementia, pre-Alzheimer's disease, Alzheimer's disease, epilepsy, Pick's disease ), Huntington's disease, Parkinson's disease, Lou Gehrig's disease, pre-dementia syndrome, Lewy body dementia dementia, dentate erythropollidus Lewy body atrophy, Freidreich's ataxia, multiple system atrophy, type 1, type 2, type 3, type 6, type 7 spinocerebellar ataxia, amyotrophic lateral sclerosis, familial spastic paralysis, Spinal muscular atrophy, spinal bulbar muscular atrophy, age-related cognitive decline, cognitive decline, moderate mental impairment, due to aging, conditions affecting brainwave intensity and/or brain glucose utilization, stress, anxiety, attention Mental decline, mood deterioration, general cognitive performance and mental health, neurodevelopment, neurodegenerative disorders, hormonal disorders, neurological imbalances, or any combination thereof due to impaired concentration and attention. In a specific embodiment, the cognitive disorder is memory impairment.

In some embodiments, an effective amount of a compound or composition described above is administered to a subject in need thereof to inhibit, prevent or treat inflammation or an inflammatory disease. In some embodiments, the inflammation or inflammatory disease is selected from organ transplant rejection; reoxygenation injury caused by organ transplantation (see Grupp et al, J. Mol. Cell. Cardiol. 31:297-303 (1999) ), including but not limited to transplantation of the following organs: heart, lung, liver, and kidney; chronic inflammation of joints, including arthritis, rheumatoid arthritis, osteoarthritis, and bone diseases associated with increased bone resorption; inflammatory Bowel disease (IBD), such as ileitis, ulcerative colitis (UC), Barrett's syndrome, and Crohn's disease (CD); inflammatory lung disease, such as asthma, acute respiratory distress syndrome (ARDS) and chronic obstructive pulmonary disease (COPD); inflammatory diseases of the eye, including corneal dystrophy, trachoma, onchocerciasis, uveitis, sympathetic ophthalmia, and endophthalmitis; chronic inflammation of the gums, including gingivitis and periodontitis; inflammatory diseases of the kidney, including uremic complications, glomerulonephritis, and nephropathy; inflammatory diseases of the skin, including sclerosing dermatitis, psoriasis, and eczema; inflammatory diseases of the central nervous system, Including chronic demyelinating diseases of the nervous system, multiple sclerosis, AIDS-related neurodegeneration and Alzheimer's disease, infectious meningitis, encephalomyelitis, Parkinson's disease, Huntington's disease, epilepsy, amyotrophic Lateral sclerosis and viral or autoimmune encephalitis, pre-convulsions; chronic liver failure, brain and spinal cord injury, and cancer. Inflammatory diseases can also be systemic inflammation of the body, such as gram-positive or gram-negative shock, hemorrhagic or anaphylactic shock, or shock induced by cancer chemotherapy in response to proinflammatory cytokines, such as with proinflammatory cytokines. Cytokine-related shock. This shock can be induced, for example, by chemotherapeutic agents administered as cancer treatment. Other conditions include depression, obesity, allergic disease, acute cardiovascular events, muscle wasting disease, and cancer cachexia. Inflammation caused by surgery and trauma can also be treated with phospholipid compositions.

In some embodiments, the effective amount includes about 0.1 to about 5 grams of the krill phospholipid composition, preferably about 0.2 to about 3 grams of the krill phospholipid composition, and most preferably about 0.5 to about 1.5 grams of the krill phospholipid composition thing.

The krill phospholipid compositions of the present invention can be used to treat a variety of subjects. Suitable subjects include humans as well as domestic animals, non-human primates and companion animals such as dogs, cats and birds.

Example

Example 1

10.5 g of salt-free krill oil was obtained, containing about 58% neutral lipids and 40.5% phospholipids (measured by P-NMR). 1.75 grams of krill oil was placed in each of six centrifuge tubes with 7.0 grams of 95% ethanol to provide a lipid solution with 20% dry matter. The tube was shaken vigorously at room temperature and centrifuged at 4000 RPM for 4 minutes, which provided 715 x G at the top of the tube and 2000 x G at the bottom of the tube. The tubes were then left to stand at 10°C for two nights. The top light phase was removed and evaporated to dryness. The bottom heavy phase was also removed and evaporated to dryness.

The top phase volume was 92.5% of the initial solution at 20°C. The dry matter yield at 10°C was 6.27 grams or 60% of the initial dry matter. The phospholipid content of the dry matter was measured by P-NMR to be 60.8%. About 90% of the phospholipids present in the initial starting material were recovered in the upper phase. The astaxanthin ester content of the upper phase was measured to be approximately 52 ppm.

The bottom phase volume was 7.5% of the initial solution at 20°C. The dry matter yield at 10°C was 4.23 grams. The phospholipid content of the dry matter was calculated by P-NMR to be 9.65%, and the dry matter contained approximately 90% neutral lipids. The astaxanthin ester content of the bottom phase was calculated to be approximately 419 ppm.

Example 2

This example describes a method for preparing a crude krill lipid extract. 440 grams of 96% ethanol containing 10 grams of 1M HCl was added to 100 grams of powder in the reactor and stirred at 40C for 45 minutes. The reactor contents were then emptied through a filter to retain powder/solid particles. The filtered extract was evaporated under vacuum at 50C and obtained 29.7 g of dry matter (29.7% yield). The conductivity in the extract was measured to be 616 uS/cm. This method produces a crude krill lipid extract, which can then be desalted and concentrated as described elsewhere herein.

Example 3

This example describes the use of alcohol fractionation and centrifugation to prepare a krill phospholipid concentrate. 10.23 grams of desalted oil with 35.60% PL was mixed with 41 grams of 95% ethanol and shaken vigorously. The samples were then centrifuged at 6C and 4000 rpm for 4 minutes. The upper phase was collected and evaporated to obtain 6.16 g of oil (61% yield). The oil contained 54.94% PL.

Claims (22)

1. A krill lipid composition comprising: 50% to 85% w/w phospholipids; 5% to 35% w/w triglycerides; less than 1.0% w/w inorganic salts; and wherein the composition further has one or more of the following properties: The composition contains less than 5 mg N/100 g; and/or The composition contains less than 10 ppm total arsenic. 2. The composition of claim 1, wherein the composition further has one or more of the following properties: the composition comprises 2% w/w to 13% w/w free fatty acids; The composition comprises 0.5% w/w to 10% w/w lysophospholipid; The composition comprises 0.01% to 1% w/w ethyl ester; The composition is characterized by a conductivity of less than 20 μS/cm when measured using 5% dry matter in 95% ethanol. 3. The composition of claim 1, wherein the composition further has 2 or more of the following properties: The composition comprises 0.5% w/w to 10% w/w lysophospholipid; The composition comprises 0.01% to 1% w/w ethyl ester; and The composition is characterized by a conductivity of less than 20 μS/cm when measured using 5% dry matter in 95% ethanol. 4. The composition of claim 1, wherein the composition has the following properties: The composition comprises 0.5% w/w to 10% w/w lysophospholipid; the composition comprises 0.01% to 1% w/w ethyl ester; and The composition is characterized by a conductivity of less than 20 μS/cm when measured using 5% dry matter in 95% ethanol. 5. An oral delivery vehicle comprising the composition of any one of claims 1-4. 6. The oral delivery vehicle of claim 5, wherein the vehicle is a soft gel capsule. 7. A functional food comprising the composition of any one of claims 1 to 4. 8. A nutritional supplement comprising the composition of any one of claims 1-4. 9. A composition comprising the composition of any one of claims 1 to 4 in combination with a second nutritional ingredient. 10. A composition comprising: - the krill lipid composition of any one of claims 1 to 4; and - a carrier selected from the group consisting of vegetable oil, fish oil, krill oil, maltodextrin, calcium carbonate, dicalcium phosphate, tricalcium phosphate, microcrystalline cellulose, dextrose, rice flour, magnesium stearate, stearic acid , croscarmellose sodium, sodium starch glycolate, crospovidone, sucrose, vegetable gum, lactose, methylcellulose, povidone, carboxymethylcellulose, corn starch, and combinations thereof. 11. A dietary supplement comprising the composition of any one of claims 1-4. 12. A krill lipid composition comprising: 30% to 50% w/w phospholipids; 32% to 52% w/w triglycerides; less than 1.0% w/w inorganic salts; and wherein the composition further has one or more of the following properties: The composition contains less than 5 mg N/100 g; and/or The composition contains less than 10 ppm total arsenic. 13. The composition of claim 12, wherein the composition further has one or more of the following properties: the composition comprises 2% w/w to 13% w/w free fatty acids; The composition comprises 0.5% w/w to 10% w/w lysophospholipid; The composition comprises 0.01% to 1% w/w ethyl ester; The composition is characterized by a conductivity of less than 20 μS/cm when measured using 5% dry matter in 95% ethanol. 14. The composition of claim 12, wherein the composition further has 2 or more of the following properties: The composition comprises 0.5% w/w to 10% w/w lysophospholipid; The composition comprises 0.01% to 1% w/w ethyl ester; and The composition is characterized by a conductivity of less than 20 μS/cm when measured using 5% dry matter in 95% ethanol. 15. The composition of claim 12, wherein the composition has the following properties: The composition comprises 0.5% w/w to 10% w/w lysophospholipid; the composition comprises 0.01% to 1% w/w ethyl ester; and The composition is characterized by a conductivity of less than 20 μS/cm when measured using 5% dry matter in 95% ethanol. 16. An oral delivery vehicle comprising the composition of any one of claims 12-15. 17. The oral delivery vehicle of claim 16, wherein the vehicle is a soft gel capsule. 18. A functional food comprising the composition of any one of claims 12 to 15. 19. A nutritional supplement comprising the composition of any one of claims 12-15. 20. A composition comprising the composition of any one of claims 12 to 15 in combination with a second nutritional ingredient. 21. A composition comprising: - the krill lipid composition of any one of claims 12 to 15; and - a carrier selected from the group consisting of vegetable oil, fish oil, krill oil, maltodextrin, calcium carbonate, dicalcium phosphate, tricalcium phosphate, microcrystalline cellulose, dextrose, rice flour, magnesium stearate, stearic acid , croscarmellose sodium, sodium starch glycolate, crospovidone, sucrose, vegetable gum, lactose, methylcellulose, povidone, carboxymethylcellulose, corn starch, and combinations thereof. 22. A dietary supplement comprising the composition of any one of claims 12-15.